AU2007240860A1 - Novel heteroaryl-substituted arylaminopyridine derivatives as MEK inhibitors - Google Patents
Novel heteroaryl-substituted arylaminopyridine derivatives as MEK inhibitors Download PDFInfo
- Publication number
- AU2007240860A1 AU2007240860A1 AU2007240860A AU2007240860A AU2007240860A1 AU 2007240860 A1 AU2007240860 A1 AU 2007240860A1 AU 2007240860 A AU2007240860 A AU 2007240860A AU 2007240860 A AU2007240860 A AU 2007240860A AU 2007240860 A1 AU2007240860 A1 AU 2007240860A1
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- substituted
- hydrogen
- unsubstituted
- atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- 125000000217 alkyl group Chemical group 0.000 claims description 116
- 239000001257 hydrogen Substances 0.000 claims description 101
- 229910052739 hydrogen Inorganic materials 0.000 claims description 101
- 150000001875 compounds Chemical class 0.000 claims description 99
- 125000003118 aryl group Chemical group 0.000 claims description 94
- 238000000034 method Methods 0.000 claims description 85
- 125000001072 heteroaryl group Chemical group 0.000 claims description 77
- 150000002431 hydrogen Chemical group 0.000 claims description 72
- 125000004429 atom Chemical group 0.000 claims description 66
- -1 C3-C10 - cycloalkyl Chemical group 0.000 claims description 56
- 201000010099 disease Diseases 0.000 claims description 40
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 40
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 34
- 206010028980 Neoplasm Diseases 0.000 claims description 33
- 125000000623 heterocyclic group Chemical group 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 230000003463 hyperproliferative effect Effects 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 201000011510 cancer Diseases 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
- 238000011282 treatment Methods 0.000 claims description 23
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 20
- 241000124008 Mammalia Species 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 17
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- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 12
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- 230000004054 inflammatory process Effects 0.000 claims description 10
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- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
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- 239000003937 drug carrier Substances 0.000 claims description 6
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
- 239000002904 solvent Substances 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 24
- 238000001914 filtration Methods 0.000 description 21
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- 229910052786 argon Inorganic materials 0.000 description 20
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- XPPXHAOZWPYYAJ-UHFFFAOYSA-N 3-anilinopyridine-4-carboxylic acid Chemical class OC(=O)C1=CC=NC=C1NC1=CC=CC=C1 XPPXHAOZWPYYAJ-UHFFFAOYSA-N 0.000 description 16
- 239000012043 crude product Substances 0.000 description 16
- 239000000706 filtrate Substances 0.000 description 16
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 108090000744 Mitogen-Activated Protein Kinase Kinases Proteins 0.000 description 15
- 102000004232 Mitogen-Activated Protein Kinase Kinases Human genes 0.000 description 15
- 235000019441 ethanol Nutrition 0.000 description 13
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 13
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- CTOOKLLGWHNPED-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)pyridine-4-carbohydrazide Chemical compound NNC(=O)C1=CC=NC=C1NC1=CC=C(I)C=C1F CTOOKLLGWHNPED-UHFFFAOYSA-N 0.000 description 12
- LKJJUICFLVYDJQ-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=C1NC1=CC=C(I)C=C1F LKJJUICFLVYDJQ-UHFFFAOYSA-N 0.000 description 12
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- 239000002244 precipitate Substances 0.000 description 12
- 238000002953 preparative HPLC Methods 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 101710146526 Dual specificity mitogen-activated protein kinase kinase 1 Proteins 0.000 description 11
- 102100031480 Dual specificity mitogen-activated protein kinase kinase 1 Human genes 0.000 description 11
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Applications Claiming Priority (3)
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| US79307306P | 2006-04-19 | 2006-04-19 | |
| US60/793,073 | 2006-04-19 | ||
| PCT/US2007/009456 WO2007123936A1 (en) | 2006-04-19 | 2007-04-18 | Novel heteroaryl-substituted arylaminopyridine derivatives as mek inhibitors |
Publications (1)
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| AU2007240860A1 true AU2007240860A1 (en) | 2007-11-01 |
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| AU2007240860A Abandoned AU2007240860A1 (en) | 2006-04-19 | 2007-04-18 | Novel heteroaryl-substituted arylaminopyridine derivatives as MEK inhibitors |
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| EP (1) | EP2013180A1 (enExample) |
| JP (1) | JP5525812B2 (enExample) |
| KR (1) | KR20090005195A (enExample) |
| CN (2) | CN101426766B (enExample) |
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| MX (1) | MX2008013308A (enExample) |
| WO (1) | WO2007123936A1 (enExample) |
| ZA (1) | ZA200807263B (enExample) |
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| WO2007123939A2 (en) * | 2006-04-19 | 2007-11-01 | Laboratoires Serono S.A. | Novel arylamino n-heteraryls as mek inhibitors |
| EP2231636B1 (en) * | 2007-12-07 | 2011-09-14 | Novartis AG | Pyrazole derivatives and use thereof as inhibitors of cyclin dependent kinases |
| US9084781B2 (en) | 2008-12-10 | 2015-07-21 | Novartis Ag | MEK mutations conferring resistance to MEK inhibitors |
| WO2011106298A1 (en) | 2010-02-25 | 2011-09-01 | Dana-Farber Cancer Institute, Inc. | Braf mutations conferring resistance to braf inhibitors |
| BR112012022801B8 (pt) | 2010-03-09 | 2019-10-29 | Dana Farber Cancer Inst Inc | método de identificar um indivíduo que tem câncer que é provável beneficiar-se do tratamento com uma terapia de combinação com um inibidor de raf e um segundo inibidor e uso de um inibidor de raf e um segundo inibidor para a fabricação de um medicamento para tratar câncer |
| US9133123B2 (en) | 2010-04-23 | 2015-09-15 | Cytokinetics, Inc. | Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use |
| AR081331A1 (es) | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
| AR081626A1 (es) | 2010-04-23 | 2012-10-10 | Cytokinetics Inc | Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos |
| US8759380B2 (en) | 2011-04-22 | 2014-06-24 | Cytokinetics, Inc. | Certain heterocycles, compositions thereof, and methods for their use |
| US20150141470A1 (en) | 2012-05-08 | 2015-05-21 | The Broad Institute, Inc. | Diagnostic and treatment methods in patients having or at risk of developing resistance to cancer therapy |
| WO2014007228A1 (ja) | 2012-07-03 | 2014-01-09 | 小野薬品工業株式会社 | ソマトスタチン受容体作動活性を有する化合物およびその医薬用途 |
| KR20170125931A (ko) * | 2015-03-10 | 2017-11-15 | 오리진 디스커버리 테크놀로지스 리미티드 | 면역조절제로서의 3-치환된 1,3,4-옥사다이아졸 및 티아다이아졸 화합물 |
| TN2017000483A1 (en) | 2015-05-20 | 2019-04-12 | Amgen Inc | Triazole agonists of the apj receptor. |
| WO2017033113A1 (en) | 2015-08-21 | 2017-03-02 | Acerta Pharma B.V. | Therapeutic combinations of a mek inhibitor and a btk inhibitor |
| US10150754B2 (en) * | 2016-04-19 | 2018-12-11 | Celgene Quanticel Research, Inc. | Histone demethylase inhibitors |
| WO2017192485A1 (en) | 2016-05-03 | 2017-11-09 | Amgen Inc. | Heterocyclic triazole compounds as agonists of the apj receptor |
| WO2018097945A1 (en) | 2016-11-16 | 2018-05-31 | Amgen Inc. | Heteroaryl-substituted triazoles as apj receptor agonists |
| US10906890B2 (en) | 2016-11-16 | 2021-02-02 | Amgen Inc. | Triazole phenyl compounds as agonists of the APJ receptor |
| WO2018093580A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Triazole pyridyl compounds as agonists of the apj receptor |
| EP3541792B1 (en) | 2016-11-16 | 2020-12-23 | Amgen Inc. | Triazole furan compounds as agonists of the apj receptor |
| MA46827A (fr) | 2016-11-16 | 2019-09-25 | Amgen Inc | Composés de triazole à substitution cycloalkyle en tant qu'agonistes du récepteur apj |
| US11191762B2 (en) | 2016-11-16 | 2021-12-07 | Amgen Inc. | Alkyl substituted triazole compounds as agonists of the APJ Receptor |
| WO2018204532A1 (en) | 2017-05-03 | 2018-11-08 | Vivace Therapeutics, Inc. | Non-fused tricyclic compounds |
| JP7245229B2 (ja) | 2017-08-21 | 2023-03-23 | ビバーチェ セラピューティクス,インク. | ベンゾスルホニル化合物 |
| WO2019089335A1 (en) | 2017-11-03 | 2019-05-09 | Amgen Inc. | Fused triazole agonists of the apj receptor |
| EP3720430A4 (en) | 2017-12-06 | 2021-05-05 | Vivace Therapeutics, Inc. | BENZOCARBONYL COMPOUNDS |
| BR112020011162A2 (pt) * | 2017-12-07 | 2020-11-17 | Amplyx Pharmaceuticals, Inc. | agentes antifúngicos derivados de piridina substituída por heterociclo |
| CN110317190A (zh) * | 2018-03-28 | 2019-10-11 | 首都医科大学 | 一种三唑-羧酸酯类衍生物在医药领域的应用 |
| WO2019213006A1 (en) | 2018-05-01 | 2019-11-07 | Amgen Inc. | Substituted pyrimidinones as agonists of the apj receptor |
| EP3793551A4 (en) | 2018-05-16 | 2022-01-26 | Vivace Therapeutics, Inc. | OXADIAZOLE COMPOUNDS |
| AU2020242287A1 (en) | 2019-03-21 | 2021-09-02 | INSERM (Institut National de la Santé et de la Recherche Médicale) | A Dbait molecule in combination with kinase inhibitor for the treatment of cancer |
| KR20220098759A (ko) | 2019-11-08 | 2022-07-12 | 인쎄름 (엥스띠뛰 나씨오날 드 라 쌍떼 에 드 라 흐쉐르슈 메디깔) | 키나제 억제제에 대해 내성을 획득한 암의 치료 방법 |
| EP4061364A4 (en) * | 2019-11-20 | 2023-09-13 | Vivace Therapeutics, Inc. | HETEROARYL COMPOUNDS |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| JP2024521788A (ja) | 2021-05-27 | 2024-06-04 | ミラティ セラピューティクス, インコーポレイテッド | 併用療法 |
| WO2025054260A1 (en) * | 2023-09-07 | 2025-03-13 | Kinnate Biopharma Inc. | Inhibitors of mek kinase |
| WO2025073765A1 (en) | 2023-10-03 | 2025-04-10 | Institut National de la Santé et de la Recherche Médicale | Methods of prognosis and treatment of patients suffering from melanoma |
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| IL144215A0 (en) | 1999-01-13 | 2002-05-23 | Warner Lambert Co | 1-heterocycle substituted diarylamines |
| GB2373245A (en) * | 2001-03-12 | 2002-09-18 | Bayer Ag | Pyridinyl pyrazoles and their use for the treatment of COPD |
| CA2498281A1 (en) * | 2002-09-10 | 2004-03-25 | Pharmacia Italia S.P.A. | Substituted pyridine derivatives as antitumor agent |
| AU2003293376A1 (en) * | 2002-12-10 | 2004-06-30 | Imclone Systems Incorporated | Anti-angiogenic compounds and their use in cancer treatment |
| US20050004186A1 (en) | 2002-12-20 | 2005-01-06 | Pfizer Inc | MEK inhibiting compounds |
| AU2004229392A1 (en) * | 2003-04-09 | 2004-10-28 | Exelixis, Inc. | Tie-2 modulators and methods of use |
| WO2005000818A1 (en) | 2003-06-27 | 2005-01-06 | Warner-Lambert Company Llc | 5-substituted-4-`(substituted phenyl)!amino!-2-pyridone deviatives for use as mek inhibitors |
| WO2005004818A2 (en) * | 2003-07-09 | 2005-01-20 | Imclone Systems Incorporated | Heterocyclic compounds and their use as anticancer agents |
| JP4768628B2 (ja) | 2003-11-19 | 2011-09-07 | アレイ バイオファーマ、インコーポレイテッド | Mekの二環系阻害剤及びその使用方法 |
| PT1802579E (pt) * | 2004-10-20 | 2014-02-17 | Merck Serono Sa | Derivados da 3-arilaminopiridina |
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- 2007-04-18 KR KR1020087028187A patent/KR20090005195A/ko not_active Withdrawn
- 2007-04-18 MX MX2008013308A patent/MX2008013308A/es not_active Application Discontinuation
- 2007-04-18 BR BRPI0711625-0A patent/BRPI0711625A2/pt not_active IP Right Cessation
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- 2007-04-18 WO PCT/US2007/009456 patent/WO2007123936A1/en not_active Ceased
- 2007-04-19 AR ARP070101677A patent/AR060807A1/es unknown
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2008
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Also Published As
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| EP2013180A1 (en) | 2009-01-14 |
| MX2008013308A (es) | 2008-10-27 |
| ZA200807263B (en) | 2009-11-25 |
| US20070287737A1 (en) | 2007-12-13 |
| CN103121996B (zh) | 2015-10-21 |
| US8076486B2 (en) | 2011-12-13 |
| AR060807A1 (es) | 2008-07-16 |
| WO2007123936A1 (en) | 2007-11-01 |
| JP2009534386A (ja) | 2009-09-24 |
| CA2644425A1 (en) | 2007-11-01 |
| IL194546A0 (en) | 2009-08-03 |
| JP5525812B2 (ja) | 2014-06-18 |
| HK1127354A1 (en) | 2009-09-25 |
| EA200802050A1 (ru) | 2009-04-28 |
| KR20090005195A (ko) | 2009-01-12 |
| CN103121996A (zh) | 2013-05-29 |
| CN101426766A (zh) | 2009-05-06 |
| BRPI0711625A2 (pt) | 2011-12-06 |
| CN101426766B (zh) | 2014-03-26 |
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